Canadian Branding Entrepreneur: Rubs Elbows with the Stars

By Angus Gillespie

Toronto has often been tagged with the nickname “Hollywood North” given the number of big-screen movies and television programs that are filmed within Canada’s most populous city.  However, there is at least one highly successful entrepreneur working behind the scenes in the Greater Toronto Area who has a direct connection with some of Hollywood’s biggest stars.

That individual is 40-year-old Jesse DeCosta, who runs DeCosta Marketing Inc.  A significant aspect of DeCosta’s brand management and licensing company centres on some of the big name celebrities he represents south of the border.  They include the likes of Michael Jackson’s family as well as actors and comedians Will Smith, Kevin James and Jamie Foxx.   Also in DeCosta’s stable are: Donna Karan, Leah Remini, Jordan Knight, Wayne Brady and Kristoff St. John.  The funny thing is, he lives in southern Ontario in virtual anonymity and yet he’s extremely well known in southern California by some of the premier celebrities in the world.

DeCosta, who has a staff of 15, works out of his beautiful home in Mississauga where he lives with his wife Sandra and their two daughters, who are 11 and 9.  Jesse met his wife at a family Christmas party in 1989.  They were together for many years and married in 1996. He’s only worked out of his home for the past two years after being convinced by others that he really did not need a downtown Toronto office when the vast majority of his clients are in Los Angeles, where he does maintain an office.  Dropping the Toronto office also represented a savings of about $14,000 a month on rent. 

As you’d expect, DeCosta has a very engaging, outgoing personality, which of course serves him well in his career.  What makes his story that much more incredible is the fact he’s had to earn everything the hard way, starting from extremely humble beginnings to a lifestyle now that most people could only dream about.

Early Life

DeCosta’s story actually began in Dar es Salaam, Tanzania, which is where he was born.  The situation was worsening politically in east Africa in 1974 and Jesse’s father decided it was best to leave.  It is one thing to have to start from humble beginnings, but DeCosta and his family had to first overcome danger in their homeland and then overcome the adversity and fear of the unknown in moving to a strange new country with no appreciable financial means with which to survive. 

“They at first decided to go to the United States,” DeCosta says of his parents’ decision.  “But I know my dad was advised to go to Canada instead, so we originally went to Toronto but the immigration officer said Edmonton was booming and that was the place to go.”  But those early days in the Alberta capital were anything but easy.  “My dad took us out there but we had no place to stay and were in a little motel for two months before we got a little place and my father worked for a time as a draftsman.” 

But it was tough for the family in Edmonton, where Jesse’s dad had been unable to hold down stable work for a long period of time, so he opted to see what was available in Toronto while leaving the rest of the family at home, thousands of kilometres away.   Jesse’s dad managed to find a job, but sadly he died soon thereafter of a heart attack, even before the rest of the family was able to move east and join him. 

“We were in a very bad financial situation and I found out later after my mom passed away, which was a few years ago, that we actually had nothing,” DeCosta reveals.  “The bank took the house so my mom had no choice but to move us to Toronto.  We were all living in a one-room apartment in Scarborough and our clothes were in garbage bags.  But my mom always had a smile on her face and somehow we got by.”

That positive attitude exhibited by his mother was obviously passed on to her son, as Jesse began exhibiting an entrepreneurial spirit at a very young age.

“I started working when I was 16 drawing caricatures at theme parks to make money and I put myself through college but I couldn’t go to university; we just didn’t have the money,” DeCosta says.  He took Graphic Design at George Brown College in Toronto and still remains at the forefront when it comes to the design aspect when working with his clients.

Upwards and Onwards

Very early in his career at the age of 18 in 1989, DeCosta gained valuable experience working for Sony Music and a company called Microform, where he was the very first employee on the services side of the business, which until then had been involved primarily in media duplication.  The services side wound up growing to a peak staff of more than 500. 

The big break came in 1999 when his lawyers connected DeCosta with the legal representatives of Canadian R&B singer-songwriter Deborah Cox. 

“Our lawyers and her lawyers knew each other,” DeCosta reveals.  “At the time the Internet was still kind of new and my lawyer said he knew a guy who is working in media entertainment.  I was working at my first company which was primarily in Internet marketing and advertising for Canadian artists and entertainers.” DeCosta’s career really escalated into another stratosphere altogether in terms of success when he was able to land a working relationship with Will Smith, whose diversified talent helped rocket him to fame as a musician, actor and comedian.

“Who you see is who you get,” DeCosta says when discussing his good friend.  “My background with Will started with a bridge from Deborah Cox who had two managers and one of them started managing Will around the time Men in Black 2 came out.  He liked what we had been doing, including a live webcast we did for Deborah Cox back in the ’90s, even although of course nobody had a powerful enough computer to actually see anything,” DeCosta laughs. 

Jackson Family Website

One major project DeCosta recently picked up was to develop an official website for Michael Jackson’s family.

“We had a meeting with Jackie Jackson along with a business partner of mine named Rick Barlowe,” DeCosta tells us.  “Rick manages the estate of Tupac Shakur and Notorious B.I.G. and his wife grew up with Janet Jackson and there had been word the Jackson family needed help, and were looking for a team to take on their brand and manage them in a holistic way.”

After an excellent first meeting, DeCosta and his group met with Jackie Jackson for a second time in Las Vegas and it was at that point where it was determined the best approach was to develop an official website, which is exactly what DeCosta had hoped to hear.  A primary motivator for the Jackson family was to deal with many public misconceptions and also to be able to keep in touch directly with their fans.  A third meeting in Los Angeles resulted in many Jackson family members attending, including Michael’s mother and his siblings.  Many offered their opinions as to what they’d like to see on the site, which can be found at It’s an incredible site with loads of multimedia, including video concert footage.  The site will continue to grow and evolve based on the information the family wants to share with the public. 

DeCosta has no sales people working for him, saying this type of business just doesn’t work that way.  Obtaining new clients is generated through word of mouth from others who are pleased with the results. So, the vast majority of his clients have come via referral from others.  Hollywood is a very tight-knit community and it’s not easy to get within that inner circle and gain the trust of those involved.  Once inside, it’s imperative to be able to keep a number of things confidential, i.e. keep your mouth shut.   

As successful as his company has become, DeCosta would definitely like to see his list of clients continue to grow.  “Some of the greats that I would love to have one day would be Gary Oldman and Robert DeNiro; those are classic actors,” he tells us.  When asked if he’d have an interest in representing Canadian talent, DeCosta responded with a resounding “Yes.”

“But the reality is finding them, and do they want us?” he continues. “We get up and comers in Los Angeles calling us all the time but we have never gotten a call from an artist in Canada.”

We asked DeCosta whether his company would take on tougher celebrity client projects such as Lindsay Lohan, who obviously has had more than her share of negative media publicity, virtually all of it self-imposed.  DeCosta says it’s vital to be very careful about whether or not to form a business alliance with certain well-known, albeit troubled celebrities because it’s also his business reputation on the line.

“We’ve had those situations where we meet some interesting characters and it just doesn’t work out,” DeCosta grins, but not providing any names.  “It actually sorts itself out because you come to learn it’s not always just them but it could be their entire infrastructure that has cracks.  If it’s a branding or perception issue, we want to take it on.  But if they themselves are self-destructive, we can’t help that because no amount of branding in the world is going to hide the truth.” 

The DeCosta Marketing model incorporates a complete management system, including the licensing of their clients’ brand and introducing them to new markets and generating new revenue by creating innovative themes for fans.

Family Ties

One of the perks of being in this line of business is that DeCosta has been able to take his family to southern California and see Hollywood up close.  “My kids love So Random on the Disney Channel and my daughter wanted to meet Selena Gomez.  When they were much younger they wanted to go to Nickelodeon to see how the cartoon shows were made like SpongeBob SquarePants and Dora the Explorer so we got to take them into the studios to meet the creators.  My wife is a big fan of The Young and the Restless and we have clients on the show, so she got to meet some of them during taping. It’s how I build back some brownie points after travelling so much,” DeCosta chuckles.

There has been no shortage of offers for DeCosta to move south of the border, but he’s resisted each and every time and by all accounts will continue to do so.  He’s been asked by his clients who have offered to help with the relocation process, but he and his family are happy right where they are.

“My wife was born in Mississauga and is a staunch Canadian, and so am I,” DeCosta proudly states. “You can’t replace home.” As for a daily routine, there isn’t one.  Each day is different in terms of structure.  DeCosta does get up at 5 am every day and then cooks breakfast for his children, but after that, all bets are off in terms of what he may be doing at any given day or time. His one other aspiration is to open a restaurant one day.

“I love being with people and food is the common thing with us all, we all have to eat, and to create an experience that way would be a great treat.”  There are lots of restaurants but there’s always room for one more,” he smiles.

Unforgettable Encounter

As you’d expect with someone living DeCosta’s jet-setting career, he has a number of humorous anecdotes based on bizarre encounters with some very well-known people looking to improve their public image through positive branding.  But there’s one that still makes him laugh out loud some 12 years later.

“When my career was starting off heavily in entertainment, which was around the time I met Will Smith, our name was really getting out there because of Will,” DeCosta says.  “We hooked up with Tiger Woods’ manager and he said ‘I have a client for you and I’d like you to meet with her’ and then I said ‘HER? But what about HIM?’ to which the manager responded by saying no, no, no, he’s off limits.”  So, DeCosta flew down to New York later that day to meet with this mystery female and her manager over dinner, curious as to who it could be.  When he arrived at the little restaurant in Soho, Woods’ manager was waiting alone, so DeCosta sat down and asked about the woman’s whereabouts, to which the manager responded by saying she’d be joining them momentarily.

“There’s nobody else in the restaurant, just me and Tiger Woods’ manager, and it’s around dinner time when I see a taxi pull up,” DeCosta recalls.  “Then, out of the cab steps Monica Lewinsky! She comes in and sits down with us and I’m in total shock.  I just read about her on the plane – the whole story – and there she is right in front of me!  There had to be 10,000 Chinese tourists outside the restaurant taking pictures; there were non-stop flashes.  I didn’t know what to say to her and I was really nervous, so I said ‘How’s it going?’ to which she stared back at me and said ‘Well, what do YOU think?’ and that was probably the most memorable meeting with somebody who’s in the public that I’ve ever had.”

It may be awfully hard for DeCosta to top that one.